Date: Thu, 29 Apr 2004 15:30:57 -0400
From: Kris Rice
Subject: Tales of a Crossdresser - Chapter 4
This is the continuation of the saga. I want to thank everyone for sending
me such awesome email questions. I will respond to everyone as soon as
possible. I do check them daily. I have many more chapters to go, so, please
stay tuned.
Remember, if you are offended with stories of crossdressing, sex,
lesbianism, and orgies...then WHY IS IT THAT YOU ARE JUST BY CHANCE THIS FAR
INSIDE AN EROTIC STORY LOUNGE?
Amidst all the extra time I was spending with Elaine and Bernie in
secrecy, I did manage to maintain a steady relationship throughout high
school. I was dating a beautiful girl named Autumn. She was smart, had sexy
long black hair, 5 foot 8, lean, a killer body and she did a bit of modeling
in addition to the dance classes and the cheerleading. We did many things
socially together, and were considered a great couple by our peers.
Sex, however, was indicative of how any teenage couple's sex life was;
I wanted it all the time, she didn't; I wanted to be wild, she wanted lights
off, covers up. Sure, the fact that I was banging one of my school's hottest
chicks was satisfying enough, but it was a bit of a bore. Sex with older
women was just more my speed. They accepted the fact that I liked the
lingerie they wore, even liked wearing it myself. I could never in a million
years trust Autumn with my secret...Could you imagine? If we broke up, I would
be at her mercy to not blab her mouth to every girlfriend she had that I was
a cross-dresser. I would be ruined.
I arrive early at my girlfriend's house and it was going to be about
an hour and a half before she got home, so I let myself into her house,
which was pretty much standard routine. Her mother was on the floor of the
kitchen, cleaning on her hands and knees.
"Hi Sherry." I greeted her, letting myself in. She looked up at me and I
immediately knew something was wrong. She was angry. She just glared at me.
Sherry was sweet when she wanted to be, but she always was checking up on
Autumn and I unexpectedly all the time. For an extremely petite lady, she
sure could yell pretty sternly.
"Um, what's wrong?" I asked cautiously, but expecting the worst. I didn't
however, expect what was about to happen.
She got up and came over to me, and before I even know what happened, she
slaps me across the face.
"What the heck was that for?!" I asked, shocked. My own mother never slapped
me.
"I'll tell you what that's for! Follow me!!" She yelled. I reluctantly
followed Sherry into the bathroom of the main floor hallway and she pulls
out a clear plastic baggie and throws it at me. It hit me in the chest and
sailed to the floor. I looked down at the contents and my throat clenched
up. It was an empty rubber packet, dark blue in color; my preferred brand.
"Sherry, I can explain..." Although lying would have made her even more upset,
I didn't even have to begin. She began to cry.
"I work so hard. Really I do...sniff...I try to make ends meet, clean, cook,
wash clothes, pay the bills, and what is the thanks I get?" Sob..."I get a
husband in jail for stealing cars and a fifteen year old daughter that
thinks she can fuck in my house behind my back. What's the thanks I get in
return?! Nothing!" She was crying through all the yelling
She leans towards me and thumps her hands on my chest several times in
anger. I am totally baffled as to what to do, so I just hug her as she's
mumbling under her breath. Sherry lowers herself to her knees in front of me
and with a palm, pushes my waist back as my ass presses into the vanity.
Sherry begins fumbling with my zipper of my jean shorts, pulling it down and
begins sobbing.
"Sherry, what are you doing?" I asked, staring down at her in disbelief.
"Shut up, Kris, just shut up! I haven't had a man inside me in six years,
and I'm sick of being alone. Why is my daughter the lucky one? She's only
fifteen. There's no way she needs to be fucking a seventeen year old guy
right now. Why would she be so interested in you? I have a right to know
what she is so attracted to."
I feel my cock swelling like a balloon at this point. She has one hand
inside my boxers and begins to steer me loose.
"Sherry, I don't think that we.." I stuttered.
"I said shut up! If I want to yell at you, I'll yell at you. If I want to
hit you, I'll hit you, If I want to..."
Her mouth sheathed the length of my shaft and she stopped when I reached her
throat. She bobs and slurps and devours my cock. Oh she was being so nasty.
I always looked at Sherry like Autumn's older sister rather than
mother. She had her daughter when she was only seventeen, which made her
only fifteen years older than me. For those not very `math-letic', Sherry
was thirty two. She was borderline skinny. I must tell you at this point
that I have always found Sherry to be a very attractive woman. Autumn teased
me for two weeks the day I met her mother and thought that it was her older
sister. I thought when I first met her that if I was a few years older, I
would rather be fucking Autumn's mom rather than her...I guess I didn't have
to wait.
She strips me down to my boxers, and I help her down to a red satin
bra and matching thong. She leads me to the bedroom and pushes me onto her
bed and continues to ingest my meat.
Sherry suddenly gets up and walks to the other side of the room and
leans up against the corner dresser, spreads her legs apart, and looks over
her shoulder at me.
"Can you fuck me standing up?" she asks.
"I'll do whatever you want. God, you got me so fucking hot."
"Fuck me from behind then, Kris." Sherry teased.
"I need a condom." I said.
"Don't ruin the moment and remind me. Get over here." Sherry hissed.
"But..."
"Kris, if I wanted you to wear one, I would make you wear one. I don't like
condoms. I want you over here to fuck me bareback. I've been thinking about
this for two months now. Don't ruin the moment and come here and fuck me!"
I went to her, wrapped an arm around her waist, and pulled her panties
aside and sank two fingers inside her. The only sounds in the whole house
were our increasing pants as we felt and fondled and positioned ourselves.
She gasped. I kissed her back. I hold her panties to the side and slid my
cock up and down her hole. I loved the sound of her voice. I loved hearing
that purr of her words. She had a young voice, and she holds her "S's" just
a second longer than other sounds. She hissed slightly in an innocent
manner, and it was adorable.
My fingers were soaked with slick cream from her orifice, and I pulled
her back and guided my aching erection into her lovesick, unfilled slit. She
was much tighter than her daughter. I made it three-quarters of the way in
and I hear her gasp for air.
"Holy jeez, Kris! Don't go too deep, let me adjust." She warned, but I
didn't listen. I locked hands on her slim firm hips and went in and out of
her with a bit of effort on the push and pull. She was right, she hasn't
been fucked. Six years must do a lot to a vagina, even after two kids. I had
no problem fitting in Autumn. We were like a lock and key.
Now please understand, Sherry is a tiny, wavy haired brunette; she's 5
foot 7, one hundred five pounds, and still manages to tote nice C cup
breasts and hasn't been trespassed in 6 years other than her occasional
fingers. Sherry begs me to go easy and let her hole adjust to me because I
had at least an inch of meat that wouldn't fit, and I was already bottoming
out in her.
Although fucking doggie style allows the deepest penetration, some
women are just sized differently inside. I have found out later in my teen
years and now into my mid twenties that I like women who are a little more
"frequented" when it comes to sex. I'm sorry ladies, no girl wants to feel
like she just got a visit from Roto Rooter. (please feel free to email your
comments, you all do anyway)
As I was saying, I begin to work in and out of her really nice.
Through the pounding, she is gasping with each and every thrust and really
getting me excited. She guides me back to the corner of the queen-size bed
and rides me in a reverse-cowgirl squat. I watch as her tiny ass cheeks work
around on my tool. Sherry cums quickly, crying out in pleasure and I am
finally realizing that I am fucking my girlfriend's 32 year old prim and
proper church going mother.
Sherry turns and rides my lap, and kisses me very passionately and
manages to climb the bed as I take her doggie style with one foot on the
floor. I pound her furiously, just listening to the wet noises of our loins
sliding together and her abrupt gasps for air were so erotic.
I lied on me back and Sherry rode the shit out of me. Every time I
announce I am going to cum, Sherry slows down to keep me from cumming. She
must have did this at least six times. I didn't ask her, but I knew that she
was savoring the moment with me. I didn't mind that she was using my cock.
Sherry came countless times.
I looked at the clock. Autumn was due home in one minute.
"Shit!" I yelled.
"What?" Sherry asked, her hips gyrating quicker on my lap.
"The time!" I said, "Autumn will be home any second! God Sherry, we're gonna
get caught!"
"No we're not." Was all she said.
She distracted me by deeply kissing me and making fists together with
my hands. She was rocking just slowly enough on my meat to keep me from
getting off. I tried thrusting up into her, but with our mouths locked, she
would just change the angle of penetration. I was so close, and she kept me
there for an eternity. Damn, for a woman out of practice, she sure fooled
me.
Just then, I heard stones being crunched by tires in the distance. I
knew that sound. Autumn was getting dropped off from her friend's house. The
driveway was long, but we had merely seconds left before we got caught.
"Stop, Sherry! She's home!" I yelled, trying to sit up.
She pushed my chest down and frantically rode me. In seconds, my loins
exploded inside her. Sherry's eyes widened as I felt her insides get filled
with huge blasts from my cock. I could feel the cum jetting out of me. I was
cumming hard. Sherry rode it out. After I calmed down, Sherry jumped off me
and grabbed her panties and shorts and shirt and put them on.
She tossed my clothes at me and I got from the bed to the floor. My
cock was soaked in cum. It was a race against the clock. Then, as I was
about to pull my jean shorts up, Sherry turns and puts my cock in her mouth
and our creamy evidence gets swallowed. Her saliva mixes with `us' briefly
to make a salty mouthwash.
Sherry raced to the kitchen floor where she was cleaning well over an
hour ago to pretend she was busy again, and all I could do was manage to run
to the bathroom and lock the door behind me as I heard Autumn come in
through the side entrance of the house.
I managed to wash my face, and cool myself off before exiting to
either `pass it off', or `face the music'. I still will never forget how
close we were to getting caught that evening, and that day forth, Autumn
never caught on to us. I couldn't be convinced of anything more erotic than
when the three of us hung out that evening, thinking that Autumn never knew
that my cum was seeping out of her mother.
The next day, I came over and my girlfriend Autumn was gone. Damn, I
nearly forgot, it was dance class.
"Looking for Autumn?" Sherry called from the other room.
"She's at dance, right?" I called out from across the house to her.
"Yes," she replied, "She won't be home until after seven-thirty."
"Wow, it's only five after four now..." I said as she walked down the hallway
towards me.
"I know..." she said, "You could come back if you want to." Sherry teased.
"But I didn't come here to see your daughter." I teased back.
"Well, how did I know that was what you were going to say?" Sherry said,
touching herself up onto my body and kissing me deeply.
"I couldn't stop thinking about you all day today." I admitted to her.
"I never knew a guy could cum that much," Sherry admitted, "I had to sit at
the dining room table with the two of you and I was so wet, I was leaking
through my shorts."
Sherry took me to her daughter's bedroom, pushed me down onto the
mattress and eagerly gave me head. I yanked my clothes off as she vacuumed
my tool. She stripped off her clothes; She was wearing an emerald green bra
and panty set that I had bought for her daughter on Christmas.
She climbs on me and rode my stiff tool for an eternity on Autumn's
bed. She came at least three times. I threw her down on her back and ate her
pussy until she came twice more. I then fucked her doggy-style to more
screaming climaxes. I grunted and fucked her as hard as I possibly could. I
was jack-hammering her like a pro. Just as I was about to cum, Sherry slid
forward, turned, and swallowed my loaded tool just as I released my streams
of hot semen. Let me tell you guys, you think you cum hard? You haven't came
as hard as I did that day. After two pulses in her mouth, I shot cum out her
nose. I loved watching her eyes bulge as she choked it all down when it
surged into her awaiting mouth. If I could keep one gift in my life, it
would definitely have to be the ability to do that to a chick.
Next weekend Sherry takes me to a popular hotel chain and has a video
camera set up there. She wants to film us and watch it over and over again.
She strips to a purple silk camisole, matching g-string and white stay-up
thigh highs. I figured I had nothing to lose with admitting to Sherry my
fetish.
I went to the bathroom of the motel and put on a black crochet pothole
body-stocking and headed out to the room. At first, Sherry's eyebrows were
high in the air at the sight of me. I told her I'd remove it if she wanted
me to. She said she didn't care. She said she actually thought it would be
sexy to fuck me with it on. I was absolutely shocked. I figured that it just
may be all or nothing again. I ate her pussy immediately, holding her
writhing hips down as I sucked her clit and tongued her hole and she
screamed out for me to fuck her right away.
"Fuck me right now, Kris, I can't wait!" Sherry said, spreading her legs
wide and far. I climbed up to her fast. She threw her stocking clad calves
up on my shoulders and I sank into her tight little pussy. I was hammering
her at lightning pace. She was more than bent in half. Her ass was off the
bed, I was hovering over her. She held my stocking covered ass as I pounded
her hard.
I never felt so close to a woman in my whole life. I wanted to be
inside her forever. I wanted to fuck her over and over again. She was
perfect for me. The bad thing was that I was fucking my girlfriend's mom.
This was so nasty, but so good as well. She never complained, she never
hesitated, she just acted it out. She never second guessed the times we
spent together, or really was concerned of the consequences; she was just
really happy to get a fucking from a seventeen year old guy.
This afternoon, there was a witness; the camera. It was recording our
nasty act for us to watch. For anyone to see that accidentally found it. At
first, I was worried about the tape. Then I began to think, `hey, what do
you have to lose? She's the married one...let her try to explain why she was
fucking her daughter's boyfriend for a couple of hours in a motel room who
just happened to be dressed up in a female body stocking. That got me
excited...
"I'm gonna cum, Sherry, tell me where you want it!" I groaned.
"Through a quivering voice underneath me, she cried out,
"all....over....my.......face!!!"
I pulled out of her tight bald pussy and aimed my cock straight down
at her face. When I came, I watched in awe as a huge trail of my white jelly
splattered from her chin to her nose. She reacted with a gasp and a startled
flinch. I had her trapped underneath me as the rest of my seed landed on her
face. After my balls were empty, I let her legs onto the bed and Sherry
little by little coached my semen from her face to her mouth. She cleaned up
my sticky juice and swallowed every last drop.
It seemed that even though her and I were talking together in school,
I couldn't hear what Autumn was saying. She was complaining about this
teacher, or this girl, but it was all just a bunch of shit to me. I just
wanted to fuck. All that was going through my mind was my perfect situation.
I am seventeen, and there are four women in my life that I am having sex
with; Elaine, Bernie, Autumn, and now her mother, Sherry. This was getting
crazy.
What did they find so interesting about me? Were they truly attracted
to me? Was I just a convenience for them to use? Did they like the
cross-dressing, or were they going to betray me and somehow reveal my fetish
to my family? Hell, Sherry and Autumn didn't even know about the
cross-dressing yet. Now, mind you, these were all thoughts I had after the
fact. All I did at this time was live for the moment. What ever happened,
was happening for a reason.
Sherry was a little bit paranoid that we would get caught. Not by her
daughter, we had that one covered. She was more paranoid that she would seem
different to her husband, who was in jail at the time. That he might notice
a change in her personality or character. Her and I had plenty of time to
discuss this over the coming months we were alone together. She just wanted
to be cared for, and knew she couldn't get it from me.
She was also paranoid about me being intimate with her daughter. She
was so worried that I would accidentally get her daughter pregnant. She
didn't want her daughter following in the same footsteps as she did. I also
began to think that deep down, the reason Sherry began to fuck me on a
steady basis was she wanted to wear me out so I didn't fuck her daughter
near as much.
To be honest, between Sherry during the week, and My stepmother and
her friend Bernie, I barely had enough steam to want to fuck Autumn at all.
Autumn was fine with that. We were intimate about twice a month, and the
weeks went by so fast it seemed more frequently than that.
Well, after a grueling fuck with Elaine and Bernie the following
weekend, I pitched the idea of getting Sherry into the mix one time. They
were a bit hesitant, and wanted to know what she looked like. I explained,
but they still wanted to see her somehow before anything would be
considered. That was an easy one. Sherry worked in the public's eye, so all
they had to do was visit where she worked to see her in the flesh.
"That is...unless I can get the video we made together out of her house."
"You two made a video?" Elaine asked.
"It was her idea." I defended.
"What is this thing you have with videos? You're always making them." Bernie
teased.
I told them that the hard thing was going to be pitching this to
Sherry. Elaine reassured me that things would all work out. If Sherry didn't
want to fuck around, who was she going to tell?
Elaine had one stipulation; She wanted some more guys to fuck around
with her and Bernie. I could handle that, I told them. I knew lots of guys
who didn't go to my high school that would be interested in fucking around
with some older women. I mentioned that there would be no way I was dressing
up if there were going to be other guys in the room. No Problem.
Was I going to finally have my three favorite women in the same place
to fuck? Could it be so? I was going to fantasize of a `dress-up and fuck'
party until the day it happened...